p-Toluenesulfonic acid → HCID 70106120, compound

HRID 612470Notes

Reaction equation

HRID 612470 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10]OC)=[CH:5][C:4]=1[CH3:13].[ClH:14].[NH:15]([C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)[NH2:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[ClH:14].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]=[N:16][NH:15][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:5][C:4]=1[CH3:13]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 223202584-Hydrazinylpyridine hydrochlorideHCID 54131046HCID 54131046, compound

Product 1

HCID 70106120HCID 70106120, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-methoxy-2-methyl-4-(2-methoxyvinyl)benzene (17 g) and 4-hydrazinopyridine hydrochloride (15.4 g) in ethanol (300 ml), p-toluenesulfonic acid (2.7 g) was added, with stirring. The reaction mixture was stirred under reflux for 2 hrs, filtered, and the filtrate was concentrated in vacuo. The residue was recrystallized from methanol to yield 10.9 g (39%) of product, mp 224-226° C.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureunder reflux for 2 hrs
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-ef86141e0e71487189265246e2c56f56
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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